2-<(tert-butoxycarbonyl)amino>-5-<2-(methylamino)phenyl>propan-1-ol | 168965-75-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-<(tert-butoxycarbonyl)amino>-5-<2-(methylamino)phenyl>propan-1-ol
• CAS: 168965-75-1
• 化学式: C₁₇H₂₈N₂O₃
• 分子量: 308.421
• InChiKey: SKXNOZHNGATHIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  70.59
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-<(tert-butoxycarbonyl)amino>-5-<2-(methylamino)phenyl>propan-1-ol 在 palladium on activated charcoal 2,6-二甲基吡啶 、 氢气 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 50.0h， 生成 2-{[2-(4-tert-Butoxycarbonylamino-5-hydroxy-pentyl)-phenyl]-methyl-amino}-3-methyl-butyric acid
  参考文献：
  名称：

  Synthesis, Conformation, and Biological Activity of Teleocidin Mimics, Benzolactams. A Clarification of the Conformational Flexibility Problem in Structure−Activity Studies of Teleocidins

  摘要：

  Tumor-promoter teleocidins and their active congeners (indolactams) are known to exist in an equilibrium between at least two conformational states in solution, the twist and sofa form, due to cis-trans isomerization of the amide bond and the steric effects of substituents on the nine-membered lactam ring. Benzolactam-Vs, in which the indole ring of indolactams is replaced with a benzene ring, were designed and synthesized in an attempt to reproduce the active conformation of teleocidins. Among these benzolactams, eight-membered lactams (benzolactam-V8) can only exist in the twist form, and 9- and 10-membered lactams (benzolactam-V9 and -V10) exist exclusively in the sofa form in solution. The stronger biological activity of benzolactam-V-8-310 than that of indolactam-V (IL-V) and the inactivity of benzolactam-V-9-310 for differentiation inducing activity of HL-60 clearly indicated that the twist form is close to the active conformation of teleocidins.

  DOI：

  10.1021/ja953578v
• 作为产物：
  描述：

  ethyl 2-<(tert-butoxycarbonyl)amino>-5-<2-(methylamino)phenyl>propanoate 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到2-<(tert-butoxycarbonyl)amino>-5-<2-(methylamino)phenyl>propan-1-ol
  参考文献：
  名称：

  Synthesis, Conformation, and Biological Activity of Teleocidin Mimics, Benzolactams. A Clarification of the Conformational Flexibility Problem in Structure−Activity Studies of Teleocidins

  摘要：

  Tumor-promoter teleocidins and their active congeners (indolactams) are known to exist in an equilibrium between at least two conformational states in solution, the twist and sofa form, due to cis-trans isomerization of the amide bond and the steric effects of substituents on the nine-membered lactam ring. Benzolactam-Vs, in which the indole ring of indolactams is replaced with a benzene ring, were designed and synthesized in an attempt to reproduce the active conformation of teleocidins. Among these benzolactams, eight-membered lactams (benzolactam-V8) can only exist in the twist form, and 9- and 10-membered lactams (benzolactam-V9 and -V10) exist exclusively in the sofa form in solution. The stronger biological activity of benzolactam-V-8-310 than that of indolactam-V (IL-V) and the inactivity of benzolactam-V-9-310 for differentiation inducing activity of HL-60 clearly indicated that the twist form is close to the active conformation of teleocidins.

  DOI：

  10.1021/ja953578v